Microsoft Software Engineer Jobs in Chicago, IL (NOW HIRING)

This role sits at the center of the company's technology evolution-driving how modern software is designed, built, and delivered across the business. As systems scale and customer expectations increase, the organization requires a senior technical leader who can translate complexity into resilient, high-performing solutions.
The Lead Software Engineer is responsible for elevating engineering execution, modernizing legacy platforms, and establishing scalable architecture patterns that support long-term growth. This is not a maintenance role-it is a forward-looking position focused on building systems that are secure, observable, cloud-ready, and aligned with business outcomes.
Success in this role means delivering reliable, performant applications, accelerating development through strong engineering practices, and influencing how technology drives operational efficiency and customer experience. What you'll do1. Lead software architecture and solution design

• Design and implement scalable, secure, cloud-native software solutions aligned with business objectives
• Apply API-first, modular, and service-oriented design principles across enterprise systems
• Modernize legacy applications through refactoring, re-platforming, and cloud migration strategies
• Establish architectural standards that improve maintainability, extensibility, and performance

2. Drive engineering execution and delivery excellence

• Own end-to-end delivery of complex software initiatives with a focus on quality, speed, and reliability
• Prioritize competing initiatives while maintaining high standards for performance and uptime
• Lead technical design sessions, code reviews, and development best-practice implementation
• Act as a senior escalation point for troubleshooting and production issue resolution

3. Advance cloud, DevOps, and platform capabilities

• Champion CI/CD pipelines, automated testing, and infrastructure-as-code practices
• Drive adoption of Azure services and cloud-native architectures to improve scalability and resilience
• Implement observability standards including monitoring, logging, and diagnostics
• Promote secure development practices and application-level security controls

4. Collaborate across the business

• Partner with product owners, QA, infrastructure, data, and security teams to align on delivery outcomes
• Translate complex technical concepts into clear business insights for non-technical stakeholders
• Influence roadmaps by aligning engineering capabilities with operational and customer needs
• Ensure solutions meet business, operational, and customer service expectations

5. Elevate team capability and engineering standards

• Mentor developers and raise the technical bar across the team
• Promote consistent coding standards, testing practices, and documentation discipline
• Leverage AI tools to improve developer productivity and solution quality
• Contribute to a culture of ownership, accountability, and continuous improvement

What you bring

• 8+ years of software development experience within the Microsoft technology stack
• Bachelor's degree in Computer Science, Information Technology, Engineering, or related field (or equivalent experience)
• Deep expertise in modern .NET technologies (.NET 6/7/8, ASP.NET Core, Web API, Entity Framework Core)
• Strong experience building and supporting both modern and legacy .NET applications
• 5+ years developing web applications using ASP.NET MVC/Core and modern front-end frameworks (Angular or React)
• Advanced proficiency in JavaScript, TypeScript, HTML5, and CSS
• 5+ years of Microsoft SQL Server experience, including performance tuning and database design
• Experience designing and implementing RESTful APIs and system integrations
• Hands-on experience with Microsoft Azure (App Service, Functions, Azure SQL, Storage, Application Insights)
• Experience with CI/CD pipelines (Azure DevOps, GitHub Actions, or similar)
• Strong background in automated testing, code quality practices, and observability tools
• Experience with secure coding practices and application security concepts
• Proven ability to troubleshoot complex production issues and drive resolution

Preferred qualifications

• Experience in transportation, logistics, or operational systems environments
• Exposure to microservices architecture, API gateways, and API lifecycle management
• Experience leading Agile/Scrum/Kanban teams
• Demonstrated success modernizing legacy platforms
• Experience mentoring engineers and establishing development standards

How you operate

• You think in systems, not isolated features
• You own outcomes, not just deliverables
• You make complex ideas simple and actionable
• You balance speed with stability and long-term scalability
• You challenge assumptions constructively and push for better solutions
• You communicate clearly across technical and business audiences
• You operate with urgency while maintaining engineering discipline
• You proactively identify risks and address them before they escalate

Compensation & Setup

• Pay: $120,000-$130,000 base salary
• Location: Hybrid - Downers Grove, IL
• Benefits: Comprehensive benefits package including medical, dental, vision, 401(k), and paid time off

Physical Demands and Work Environment

The physical demands and work environment described here are representative of those an employee encounters while performing the essential functions of this position. Reasonable accommodations may be made to enable qualified individuals with disabilities to perform the essential functions.

Physical Demands

• Sedentary physical activity performing non- strenuous daily activities of an administrative nature.
• While performing the duties of the job, the employee is regularly required to sit, walk, stand, reach/handle items, work with the fingers, and talk and hear others in conversations via the phone or in person.

Work Environment

• Sedentary physical activity performing non- strenuous daily activities of an administrative nature.
• While performing the duties of the job, the employee is regularly required to sit, walk, stand, reach/handle items, work with the fingers, and talk and hear others in conversations via the phone or in person.
• Up to 5% travel; occasional after-hours support based on business needs

* The above statements reflect the general details necessary to describe the principal functions of the position and are not intended to be all inclusive. The position and any of the requirements listed above are subject to change at any time according to the changing needs of the company.

* Roadrunner is an Equal Opportunity Employer and prohibits discrimination and harassment of any kind.

* We will not accept unsolicited candidates from external recruiters or recruiting agencies. Thank you!

#LI-HybridDowners Grove, IL

About Roadrunner

Roadrunner is for ambitious, smart people who excel at execution over talking about it, and who would rather invent the next standard in freight than accept the status quo.

We are looking for the Best of the Best. Action driven leaders who want to be part of real change and help design the future of LTL in the U.S. This is a place where high performers can grow, influence outcomes, and make an impact while working directly with executives and smart people from across industries.

We bring a winner mindset. We take ownership, raise the bar, and measure ourselves by results. We Run Safe. We Run Smart. We Run Together. These principles create an environment of high standards, clear ownership, and direct collaboration. We trust data over intuition, move with urgency, and hold each other accountable because winning requires it.

Roadrunner exists to prove that LTL can be better than the industry has settled for. To be the best means we need to think bigger, look outside the box, and question every assumption: too many handoffs, limited visibility, and the quiet belief that "this is just how it works." We rejected that story. We built a proprietary Smart Network for direct, long haul, metro to metro service that delivers fewer touches, faster transit, real time visibility, and genuine accountability. We are the most tech forward company in LTL, and we are not finished widening the gap.

The foundation is already strong. Recognized as one of Built In Chicago's Best Large Places to Work. Earning top marks for improvement, quality, and service. The real opportunity is still ahead: helping invent what comes next.

If you want to be evaluated among the Best of the Best and help set the new standard in LTL, we should talk.